Esters of alkamins and process of producing same.



' alcohols.

ALEX B. DAVIS, 0F INDIANAPOLIS, INDIANA, ASSIGNOR TO THE ELI LILLY ANDCOANY, OF INDIANAPOLIS, INDIANA, A CORPORATION OF INDIANA;

ESTEBS 0F ALINS AND PROCESS OF PRODUCING SE.

No Drawing.

To all whom it may concern Be it known that I, ALEX B. DAVIS, a citizenof the United States, residing at Indianapolis, Marion county, and Stateof Indiana, have invented and discovered certain new and usefulImprovements in Esters of Alkamins and Processes of Producing Same, ofwhich the following is a specification.

This invention relates to esters of alkamins which are derived from newhalogen The salts of the esters are valuable local anesthetics.

The alkamins are all derived from tertiary alcohols produced by treatingchlormethyl-w-brom-propyl ketone of the formula:

with alkyl magnesium haloids. Thus ethyl magnesium bromid produces thetertiary alcohol of the formula-- Step No. a ggpn-cm-t-cnz-cnwore-enemas He (in which may .be calleddimethyl-aminomethyl-ethyl-amyl-carbinol. These esters may berepresented by the formula Ha ta in which X and X are each alkyl orhydro gen, Y an acid radical and Z a monc=valent Specification ofLetters latent. i

Patented Aug. M, 1915.

Application filed May 22, 1914. Serial No. 840,329. 1

group, consisting, in the particular-formula, of any alkyl group.

In detail the esters of the alkamins may be formed as follows:

Step No. 3:173 parts by weight of the above described alkamin are mixedwith a considerable volume of any suitable solvent,

'the mixture heated'to boiling and 140.4

parts of benzoyl chlorid dropped in. The resulting reaction mass isplaced in a dish on the water bath, the solvent all evaporated, theresidue mixed with ten times its weight of boiling acetone, the acetonesolution thus obtained filtered and the filtrate driven ed. The residuesoon solidifies to a mass of nearly white crystals which are filteredofl" and recrystalized from acetone.

' The resulting crystalline compound probably has the followingconstitution a HCl-N and may be-called dimethylamino-methylethyl amylcarbinyl -'benzoate (carbinolbenzoyl ester) hydrochlorid. Many othercompounds of similar character may be formed by using other alkylhalogens. in.

place of ethyl bromid in Step No. 1, by using other disubstituted aminsin Step No. 2, or by using other acid haloids in Step No.

The nucleus contained in any of these cofipounds may be represented bythe forin a:--

H: -t e e (lHa in in which X and X are each alkyl or hydro- 4. Compoundscontaining the following atom group What I claim is 1. The rocess ofcondensing the halogen tertiary a cohols obtained by the action of N .35alkyl-magnesium haloids on chlor-methyltn. w-brom-propyl-ketone, withsubstituted Y amins and esterifying the resultin alkamins with an acidradical in a suitab e comk bination. 40

2. The process of treating the alkam'ms obtained by condensingchlor-methyl-ethyl- HI amyl-carbinol with substituted-amins and i H:aggllfilgngna 3331 i(ililomd to a solution of th f l g compound havingprobably h 3. The esters of alkamins represented by 0mm on, thefollowing forrnula in, o cm-cH,-d-0-d-C dH: Z-d-O-Y H: dB: H,

H: m In witness whereof, I have hereunto set 13 my hand and seal atIndianapolis, Indiana,

this sixth day of May, A. D. nineteen hundren and fourteen.

ALEX B. DAVIS. [1,. 5.] .Witnesses:

E. G. EBERHARDT, ARTHUR L. WALTERS.

gen, Y an acid radical and Z a mono-valent group capable of beingintroduced by means of the Grignard reaction.

